Iodine → HCID 86632123, compound

HRID 1510975Notes

Reaction equation

HRID 1510975 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][C:21]1[CH:22]=[C:23]([CH:31]2OCC[O:32]2)[CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].II>CC(C)=O>[C:1]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][C:21]1[CH:22]=[C:23]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH:31]=[O:32])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 807IodineHCID 68941512HCID 68941512, compound

Product 1

HCID 86632123HCID 86632123, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2.00 g (3.99 mmol) N-Boc-2-(3-{2-[2-(2-{2-aminoethoxy}ethoxy)ethoxy]ethoxy}-4,5-dimethoxyphenyl)-1,3-dioxolane 13 in 50 ml of acetone was treated with iodine (100 mg, 10% n/n) and stirred at room temperature for 60 minutes. Acetone was removed and replaced by ethyl acetate. The organic phase was washed with diluted sodium thiosulfate solution, water and brine and dried over magnesium sulfate. After removal of the solvent 1.17 g (3.74 mmol, 94%) of a slightly yellow oil remains. 1H-NMR (CDCl3) δ=9.85 (s, 1H), 7.16 (d, 1H, J=1.8 Hz), 7.13 (d, 1H, J=1.8 Hz), 5.00 (br, 1H), 4.25 (m, 2H), 3.95 (s, 3H), 3.92 (s, 3H), 3.89 (m, 2H), 3.74 (m, 2H), 3.70-3.59 (m, 6H), 3.53 (t, 2H, J=5.0 Hz), 3.30 (t, 2H, J=5.0 Hz), 1.44 (s, 9H) ppm. 13C-NMR δ=144.3, 131.6, 109.1, 106.6, 79.1, 70.8, 70.6, 70.5, 70.2, 70.1, 69.6, 69.0, 60.9, 56.2, 40.5, 28.3 ppm. MS: m/z=480 [M+Na]+, 358 [M-(COOtBuH2)]+. HRMS: Calcd. for C22H35NO9Na+480.2204, found 480.2203.

Workup

  1. customAcetone was removed
  2. washThe organic phase was washed with diluted sodium thiosulfate solution, water and brine
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-85dd92490b744ee8a4137aa5d53a3b1f
Source dataset
uspto-grants-2012_07
Patent number
US08212058B2

Reaction notes

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